Dinitroindazol dyestuffs for wool



Patented July 7, 1936 UNITEofisrsrss PATENTTOFFICE j 1 nmImorN-Dsz'on DYESTUFFS FOR WOOL Emil Senn, Basel, Switzerland, assignor to the firm of J. R. Geigy S. A., Basel, Switzerland No Drawing. Application July 22,'.I93I "S:eri'al No. 552,556. In Germany July 28, 1930 Claims. (omen-424 NO2 NO:

wherein X represents a halogen and R. represents hydrogen or an alkyl group, in presence of a solvent, with stable primary substituted hydrazines, capable of reacting, of the formula R .NH.NH2, wherein R represents a p-sulphoaryl group of the benzene series.

The condensation which takes place in this process may correspond to the following chemical equation:

OO-OR o O-OR R X +NH2NH.R1 R NH.NHR1

N0 N0, N0 N0:

B R 5 PE with X reacting with an H of the NHz-group and OR reacting, with ring-closing, with an H of the -NH-group of said hydrazines.

The new dyestuffs dye animal fibres shades which are well levelled and are distinguished by a remarkable fastness to light. The condensation may be conducted in presence of Water or of an organic solvent such as methyl or ethyl alcohol, glacial acetic acid, benzene, toluene or the like. It may be conducted with or without the addition of an acid binding agent, such as sodium acetate, potassium acetate, magnesia etc.

The following example illustrates the invention, the parts being by weight:

188 parts of para-phenylhydrazinesulphonic acid, 246.5 parts of 3:5-dinitro-2-chlorobenzoic acid and 134 parts of crystallized sodium acetate are heated together in the necessary quantity of Water for hours at 95-100 C. A deep brown reaction liquid results, fromwhic'hthe dyestufi separates in the form or a brownish-yellow precipitateo'nthe addition of mineral acid. The dyestufi is readily soluble in Water and-dyes Wool in an acid batnbeauti'fidtrown shades of remarkable fastness" to light, j K

It hastlie "following formula:

NED-T08 0 :H N 0: O 0

In this example, para-tolylhydrazinesulphonic acid or para-xyilhydrazinesulphonic acid may also be used.

It may be noted that in general also halogenated, for example chlorinated phenylhydrazine sulphonic acids can be used with a similar result. Methylor ethyl-methylesters of hydrazines are also usable. Instead of 3:5-dinitro--2- chlorobenzoic acid, there can alsobe used 3:5- dinitro-2-bromobenzoic acid, 3 :5-dim'tro-2-halogenl-methylbenzoic acid, 3 :5-dinitro-2-halogen- R N; IR

N0 No 4-ethylbenzoic acid and so on; also their methylor ethylesters may be used.

What I claim is:--

1. A process for the manufacture of brown nitrodyestufis for W001, consisting in condensing by heating aromatic dinitrobodies of the benzene series of the following constitution COOB NO NO;

wherein X represents a halogen, and R. represents hydrogen or an alkyl group, in presence of an inert solvent, with stable primary substi tuted hydrazines, capable of reacting, of the formula 'R .N H.NH2, wherein R represents a p-sulpho-aryl group of the benzene series, where- 7 V "by X reacts with a hydrogen of the NHz-group V and OR with the-NH-group of said hydrazines.

2. A process 'for "the manufacture of brown nitrodyestuifs. for W001, consisting in condensing by heating aromatic dinitrobodies of the benzene series of the following constitution wherein X represents a halogen, land R represents hydrogen or an alkyl group, in presence 7 H of an inert solvent and with addition of an acid binding agent, with'stable primary substituted nitrodyestufis for wool, consisting in condensing by heating a p-phenylhydrazine sulphonic acid in presence of an inert solvent with a 3:5 -di-V K nitro-2-halogenbenzoic acidr V 7 4. A process for the manufacture of brown nitrodyestufls for wool, consisting in condensing [by heating a chlorinated p-phenylhydrazine sulphonic acid in presence of an inert solvent V with a 3:5-dinitro-2-halogen.benzoic acid.

- 5 .-Condensati0n"productsfrom: primary substituted hydrazin'es of the benzene and naphthalene series with aromatic"2-halogen3:5-di nitrobodies of the benzeneseries,said'condensation products having the general formula 7 wherein R represents a hydrogenlor analkiyl" group, R .a"p-sulpho-aryl group of'th'e benzene series, and constituting dyestuffs-dyeing *woolin an acid bath brown shades well levelled and'remarkably fast tollight. w

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